A drill guide including an inner surface, a tip, and a deflecting device. The inner surface defines a bore extending through the drill guide. The bore is configured to individually receive therein a flexible drill bit and an insertion tool with a suture anchor mounted thereto. The tip is at a distal end of the bore and defines a tip aperture of the bore. The deflecting device is proximal to the tip and includes at least one bearing surface configured to deflect the drill bit within the bore.